


Wrecking His Innocence

by sweetheart_sam



Category: Supernatural
Genre: Alternate Universe - Student/Teacher, Bottom Dean Winchester, Boys in Skirts, Crossdressing, Loss of Virginity, M/M, Panty Kink, Student Dean Winchester, Teacher Sam Winchester, Teacher-Student Relationship, Top Sam Winchester
Language: English
Status: Completed
Published: 2019-07-13
Updated: 2019-07-13
Packaged: 2020-06-27 09:15:29
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 3,092
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19787857
Author URL: https://archiveofourown.org/users/sweetheart_sam/pseuds/sweetheart_sam
Summary: It wasn't every day that Sam invited his students to his house but Dean was different. The teenager wore pretty pink panties under his skirts he flaunted around in all day but Dean didn't know that he knew. It was an accident. He didn't mean to see up the boys skirt when he bent over in front of him to pick up a piece of paper off the floor but it happened.





	Wrecking His Innocence

Sam's hands were sweaty against his slacks that he was wearing. It was a Friday night and he was expecting a guest but he was nervous. He was a nervous man in general and he couldn't help it so when the doorbell rang, he flinched a little and got up slowly. While he made his way to the door, his heart pounded harshly against his ribcage even if he's known his guest for almost the whole year. He can't say no to his guest because if he did, he would have to face him on Monday and he's too awkward for a confrontation like that. “Mr. Wesson...hi.” His guest stood there, awkwardly, trying to find the right thing to say.

Before his guest for the night could embarrass himself anymore, Sam stepped aside and let the other male in. ”Hello, Dean.” It wasn't every day that Sam invited his students to his house but Dean was different. The teenager wore pretty pink panties under his skirts he flaunted around in all day but Dean didn't know that he knew. It was an accident. He didn't mean to see up the boys skirt when he bent over in front of him to pick up a piece of paper off the floor but it happened. “Would you like something to drink?” The air in the room was awkward and uncomfortable but Sam wanted to change that. “Yes, please. Water will be fine.” It's all Sam has so it didn't matter if he wanted something else. “You look good, by the way,” Sam said softly as he got a cup out for Dean and himself.

Both of them felt tense because of them being alone with each other. They've only been alone with each other once and that was because Dean sputtered out the courage to ask his teacher to see him outside of school. Yes, his teacher. Dean was 17 and the older man was 36. Dean wasn't even legal yet. Sam caught a glimpse of Deans cheeks heating up from the compliment and he gave a light chuckle. “T-Thank you, Mr. Wesson. You do too.” Of course, Sam did. The older man always dressed to impress even if he was only trying to impress himself. “Thank you, Dean.” With a nod of his head, Dean had a cup filled with water in his hand.

Dean was too polite, Sam decoded. Always saying “yes please”, “no thank you”, or “thank you” and the way he pronounced it was beautiful. Dean out meaning into every word he spoke even if it was a small sentence. Soon enough, the two were on Sam's couch with Sam's hand placed on Deans' bare thigh and the television was on. Neither of the men was paying attention to what was going on the television but they both tried to act like it. “Hey, if you don't mind me asking, why’d you say yes to tonight?” It was barely a whisper but Sam heard Dean. He wanted to act like he didn't her his student but then he would just be plain rude. “I said yes because I couldn't deny a pretty face like yours, now could I?” And there was a blush spreading over Deans cheeks like a wildfire. It didn't stop until five minutes later but Sam didn't seem to mind. In fact, he thought it was quite cute.

Dean cleared his throat and set his drink aside since he was nervously fiddling with the rim a moment ago. “W-Well, you could of but I really like that you didn't deny this.” As a Language teacher, Sam knew so many beautiful and expressive words to define almost anything in this world except Dean. That damned boy was a masterpiece and Sam swore to God that Dean knew that and was using it against him. Anyway, Sam needed to pay attention to the boy since he was actually in front of him. “Yeah, me too. Dinner will be ready momentarily. We can finish what we're watching and I'll fix dinner.” It wasn't a question. Sam felt a little awkward in the position he was in but he could tell Dean was feeling awkward too so he rubbed soothing circles into the top of Deans thigh with the pad of his thumb.

This is the most awkward Sam has ever felt in his life. It's not like him and Dean have talked a lot before this. Dean was one of Sam’s top students in his class, actually. They've had the occasional chat once in a while to discuss the weather outside but at the moment, neither of them knew what to say. When the timer for the burgers went off, Sam's heart leapt with happiness because then, he wouldn't be stuck in such an awkward situation anymore. “Dinner is ready, please follow me to the kitchen.” It wasn't a command but Sam used his teacher voice with Dean. It was a natural instinct now for him to talk in a more commanding way to his students.

Before he knew it, Deans hand made its way onto Sam's bicep as they walked to the kitchen. Sam cleared his throat and quickly took his arm away from Dean after Dean sat down. “I hope you don't mind that I made burgers and fries. I, um, don't get around too often so I don't know what's appropriate for first.” Shit, Sam didn't want to call this a date. That would lead Dean to think that there could actually be something between the two of them. Could there be? Yes, it was illegal for the two to have any sexual intercourse but dates and holding hands didn't seem so bad to Sam. Dean was a quiet, independent person who Sam didn't mind the presence of, even if it would be a little awkward in the beginning. “Date.” Both of them were smiling when Sam said that is was a date. Yeah, it was their first official date.

Dean licked his lips when he saw the burgers being pulled out of the small George Forman grill Sam had on his counter. His stomach growled loudly and his cheeks became as pink as his panties he was wearing underneath his black skirt. “Someones hungry. Don't worry, I’m hungry too. I forgot my lunch today since I woke up late.” The older remarked with a light chuckle as he began to make his plate. He began to make Deans plate once he know what the teenager wanted. “So, do you have a curfew or something?” Lord only knows he didn't want Dean to get in trouble with his parents. “No, actually, I don't. My parents aren't the best in the whole parenting category. They don't really care if I come home at night, I just have to message them and tell them I'm not coming home for the night. They don't care about anything.” They didn't care about their child which Sam could tell from the way Dean described them. “Well, you're always welcome here if you'd like to come over. I'm here every day and you don't have to worry about being a bother because I enjoy spending time with you.” All children should feel like they have a home and someone who cares for them.

The plates were made and Sam sat across from Dean at the table. “I really appreciate that. Maybe I'll take your offer up someday.” hopefully Dean would. They ate in comfortable silence and Sam ended up finding out that this situation he and his student were in was acceptable to him. Dean was certainly enjoying the date because he had a smile on his face even after dinner. “I enjoyed that very much. Thank you, Mr. Wesson.” Sam cleared his throat and shook his head quickly. “In my home, it's just Sam. I like either. Mr. Wesson is a little too formal and needs to stay at school.” Or in bed, Sam thought to himself. Once again, Deans cheeks heated up again and he nodded since he was too embarrassed to speak. “Come on, let's go back to the couch, yeah? I'll put on a good move.” He said in a soothing voice, not wanting Dean to completely stop speaking for the night.

Dean stood up and Sam brought their dirty plates to the sink and made a mental note to wash them later after Dean went home or wherever he would be going for the night. Sam didn't know what Deans home life was like so he didn't hope he was going home. Somewhere good for Dean. Sam walked into the living room to find Dean sitting on the couch already with his legs crossed. “Do you have a favorite movie?” Sam grabbed the remote and this time, he didn't even hesitate to lay his hand on Deans inner thigh and make slow circles in the milky flesh with the pad of his thumb. “No, I don't. I’m in the mood for a comedy though.” Dean said with a soft smile displaying on his lips. Netflix was turned on and Sam did his best to find a comedy he knew Dean would enjoy. Once he found it, he put the movie on without a second thought and Dean, without a second thought let his head rest on Sam's shoulder.

Sam liked this. He enjoyed this more than he thought he would when he opened the door to see Dean awkwardly standing there. At first, he felt that he would be taking advantage of Dean but Dean doesn't seem to be thinking that. Dean is his own person and he knows Dean well enough the teenager speaks out when he doesn't appreciate something or doesn't like it. Since Dean cross-dresses, he gets shit from guys at school but Dean doesn't take it. He's seen the way too small boy punch someone for calling him a fag.

Dean could feel Sam tense up underneath him since he was laying his head on his shoulder. He was thinking too much. “Sam? What are you thinking about?” Dean asked softly and paused the movie. Sam deserved all of his attention. “Oh, um. I was thinking about you and if I'm possibly taking advantage of you. The law probably says I am and that I'm grooming you at the moment but do you think I'm doing that? I would hate if you thought I was. You're too innocent and I don't want to be making you feel uncomfortable.” Sam tended to get a little wordy when he became nervous or had to talk about what was bothering him. Dean let out a quiet sigh and looked Sam in the eyes while taking Sam's hand into his own. “Sam, I asked you out on a date in the first place. We aren't doing anything wrong by sitting here and innocently watching tv, are we?” No, they weren't. “You know the answer is no and it will always be no. No matter what, I'm old enough to make my own choices and I want to be here on this date with you.” Dean gave Sam's hand a reassuring squeeze along with a smile.

Dean was right. Sam knew he was right too. With a shy nod of his head and a gentle squeeze to Deans hand, the movie was playing again. It began with Sam's hand skimming up Deans inner thigh under his skirt but when it turned into Dean sitting in Sam's lap, he snapped back to reality. “T-This might be a bad idea, Dean. I don't want you to feel like I could be taking advantage of you and pushing you into a decision you will regret later on.” By this point, Sam was obviously rambling on and Dean shut him up with a soft roll of their hips together. “Sam, I want to do this and you know that,” Dean whispered as he began to unbutton Sam's work shirt slowly, biting his lip as he saw Sam's chest and soft looking abs. “I promise I’ll tell you if I want to stop but I really don't.” He whispered, connecting his lips along Sam's neck.

Right now, Sam just leaned back on the couch and let this happen. Deans body felt absolutely perfect as he explored the soft skin. “Take your shirt off,” Sam growled, grabbing Deans hips as he ground his thickening cock against the soft skirt Dean was wearing. They should probably move to the bedroom so Sam stood up with Dean in his arms and carried him into the bedroom. When Dean was laid down on the bed, Dea brought his knees up and spread his legs for Sam, allowing him to see the soft white panties he wore that day. “Shit, you're trying to kill me, kid. Have you ever had sex before?” Sam was stripping himself of his clothes while he spoke to Dean.

Technically, Dean has had sex before but that was with a girl. He's never had actual sex with a guy before but he has experimented which is how he found out he was bisexual. “Um, not gay sex but I've had sex. That's not important though.” Deans cheeks heated up as he began to talk about sex with his ex-girlfriend. “Take your skirt off and lay on your stomach, legs spread, push your ass up in the air,” Sam mumbled loud enough for Dean to hear as he stripped completely and grabbed the lube from the bedside drawer. When Sam looked back at Dean, he was in position and his skirt was laid down on the bed next to his head. “Good boy. This might be a little uncomfortable but I’ll ease you into it. Just take it one finger at a time.” Sam came behind Dean and teasingly ran a hand up the back of his right thigh. “So pretty, you know that?” Sam brushed the pad of his thumb over Deans hold through the panties and listened to Dean gasp.

It was hard for Sam to not just shove three fingers into Dean but he took his time to tease him, stretch him out until he was begging so prettily under Sam. Sam was pretty sure Dean was enjoying this way too much and was close to release. “You good? You feel pretty opened but I'm pretty big.” Sam warned softly, rubbing the small of Deans back as he watched Dean nod. Slowly, Sam pulled his fingers out of Deans hole and watched his hole flutter. Dean looked so beautifully helpless, Sam thought to himself. Sam didn't waste any time lubing up his cock and pushing the tip against Deans hole. Dean has his panties just below the curve of his ass and it only made this more exciting for Sam. “Deep breath, Dean. In and out.” When Dean breathed out, that's when Sam pushed in slowly

Deans face scrunched up against the pillow but he only tried to push back even more. “Slow Dean. I don't want your first time to hurt.” Sam said a little worriedly, his left hand resting on Deans hip. As Dean took a few minutes to let Sam finally bottom out, Sam was trying not to just thrust onto him and pound him into the mattress relentlessly. “God, you feel amazing.” Sam lightly gasped out when he fully bottomed out, his balls pressing up against Deans gooch. Sam could feel Deans hole flutter around him lightly and Dean gave an experimental push back onto Sam's cock. His eyes shut tightly and his mouth hung open as pleasure rippled up his spine. “Fuck, Sam. Fuck, move, please.” Dean begged, his cock hung heavily between his legs and he began to stroke himself as Sam pulled out, lightly thrusting back into Dean.

Sam saw how well Dean reacted to the first light thrust so he didn't hesitate to thrust a little harder this time, making deans body jolt a little. “God, how are you so fucking perfect?” Sam gasped out, pressing his chest against Deans back while his hips became a little harsher. Dean gave a soft whine as he pushed back into Sam's thrusts the best he could. It washed for Dean to not cum so quickly because with Sam filling him up and his prostate being stimulated every second made it very hard for him not to lose it right then. “S’ ok, Dean. You can cum. I know you need to and fuck! I'm not close behind you.” Sam panted out, his cock twitching inside of Dean, his tip red and angry from not cumming when he needed to. 

Dean didn't need to be told twice to cum so he focused on Sam's cock pumping in and out of him and just like that, he was spilling in his hand. The tiny gasps and whines of pleasure coming from Deans pretty mouth drove Sam over the edge. A few rough snaps of his hips and he let loose inside of Dean, his cum spilling out a little as he slowly pulled out. Sam was panting as he laid down next to Dean, his arm already working to pull Dean into his chest. With a light chuckle, Sam began to speak. “That was not how I imagined this night would end.” He mumbled into Deans' hair. Sam never thought he would have sex with one of his students but yet, here he is. “You feeling ok?” Sam looked down at Dean since he didn't answer him back yet.

Deans face was slack with sleep and the older man chuckled to himself. “Goodnight to you as well, Dean.” He whispered, pressing a gentle kiss to Deans forehead as he pulled Dean closer to him. Yeah, Sam could get used to this and hopefully, Deans ass wouldn't be too sore in the morning because he didn't want his boy to be limping all day because of him, even if it did sound interesting. Sam might have to plan that for another time.

-

The next morning was sticky, for Dean. His ass had dry cum that held his cheeks together and some on his lower back but when he saw Sam and how he looked while he slept in the morning, it didn't seem to matter too much anymore. He snuggled back under Sams' neck and closed his eyes. This is something he could get used to because unlike all the dumb boys in his school, Sam was in this for the long run. Sam made sure to tell that to Dean last night when he took Deans virginity.

**Author's Note:**

> I was thinking about turning this into a series but I'm not too sure. Also, this was originally supposed to be a Cas/Dean fic but i changed with at the last minute so if you see any more mistakes, please let me know :) thanks!


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